3-Halomethylcarbonyl-9-benzoyl-1,2,3,4-tetrahydrocarbazoles

Abstract

Novel 3-Z-9-benzoyl-1,2,3,4-tetrahydrocarbazoles, wherein Z is CONR 5 R 6 , CONHOH, CN, or COCH 2 X, where X is chloro or bromo, having antimicrobial and/or anti-inflammatory activity are disclosed. Compounds wherein Z is CONR 5 R 6 and CONHOH are prepared from the corresponding 3-carboxylic acids by conversion to the corresponding acid chlorides and subsequent reaction with the appropriate amines and hydroxylamine respectively; compounds where Z is CN are prepared by the dehydration of the corresponding compounds where Z is CONH 2 ; and the compounds where Z is COCH 2 X are prepared by reacting hydrogen chloride or bromide with the corresponding compounds where Z is COCHN 2 which in turn is prepared from the corresponding 3-carboxylic acid chloride by reaction with diazomethane.

I claim: 
     
       1. A 3-Z-9-(R 3  -R 4  -benzoyl)-R 1  -R 2  -1,2,3,4-tetrahydrocarbazole having the formula: ##SPC3## wherein   Z is COCH 2  X, where R 1 , R 2 , R 3  and R 4  are each hydrogen or lower-alkyl, and X is chloro or bromo.   
     
     
       2. A compound according to claim 1 wherein X is chloro. 
     
     
       3. 3-Chloromethylcarbonyl-9-benzoyl-1,2,3,4-tetrahydrocarbazole according to claim 2. 
     
     
       4. A 3-diazomethylcarbonyl-9-(R' 3  -R' 4  -benzoyl)-R' 1  -R' 2  -1,2,3,4-tetrahydrocarbazole having the formula: ##SPC4## wherein   R' 1 , r' 2 , r' 3  and R' 4  are each hydrogen or loweralkyl.   
     
     
       5. 3-Diazomethylcarbonyl-9-benzoyl-1,2,3,4-tetrahydrocarbazole according to claim 4.